WO2013172284A1 - 光学部品の製造方法、接着組成物キット及びコーティング組成物 - Google Patents

光学部品の製造方法、接着組成物キット及びコーティング組成物 Download PDF

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Publication number
WO2013172284A1
WO2013172284A1 PCT/JP2013/063251 JP2013063251W WO2013172284A1 WO 2013172284 A1 WO2013172284 A1 WO 2013172284A1 JP 2013063251 W JP2013063251 W JP 2013063251W WO 2013172284 A1 WO2013172284 A1 WO 2013172284A1
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optical component
resin composition
reaction
curable resin
coating composition
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PCT/JP2013/063251
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English (en)
French (fr)
Japanese (ja)
Inventor
英治 片上
正浩 森本
田中　宏幸
白石　大輔
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協立化学産業株式会社
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Priority to CN201380025058.5A priority Critical patent/CN104284956A/zh
Priority to KR1020147035076A priority patent/KR102038281B1/ko
Publication of WO2013172284A1 publication Critical patent/WO2013172284A1/ja

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
    • B32B7/04—Interconnection of layers
    • B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
    • C09J5/04—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving separate application of adhesive ingredients to the different surfaces to be joined
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B2037/1253—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives curable adhesive
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2255/00—Coating on the layer surface
    • B32B2255/26—Polymeric coating
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2309/00—Parameters for the laminating or treatment process; Apparatus details
    • B32B2309/02—Temperature
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2309/00—Parameters for the laminating or treatment process; Apparatus details
    • B32B2309/04—Time
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2309/00—Parameters for the laminating or treatment process; Apparatus details
    • B32B2309/08—Dimensions, e.g. volume
    • B32B2309/10—Dimensions, e.g. volume linear, e.g. length, distance, width
    • B32B2309/105—Thickness
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2310/00—Treatment by energy or chemical effects
    • B32B2310/08—Treatment by energy or chemical effects by wave energy or particle radiation
    • B32B2310/0806—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation
    • B32B2310/0831—Treatment by energy or chemical effects by wave energy or particle radiation using electromagnetic radiation using UV radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2457/00—Electrical equipment
    • B32B2457/20—Displays, e.g. liquid crystal displays, plasma displays
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/0007—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding involving treatment or provisions in order to avoid deformation or air inclusion, e.g. to improve surface quality
    • B32B37/003—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding involving treatment or provisions in order to avoid deformation or air inclusion, e.g. to improve surface quality to avoid air inclusion
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
    • B32B37/12—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding characterised by using adhesives
    • B32B37/1284—Application of adhesive
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2312/00—Crosslinking
    • C08L2312/06—Crosslinking by radiation

Definitions

  • the present invention relates to an optical component manufacturing method, an adhesive composition kit used in the optical component manufacturing method, and a coating composition constituting the adhesive composition kit.
  • a protection panel is installed through an air layer for the purpose of protecting the glass substrate.
  • not only protective panels but also touch panels have been installed on the front of display panels.
  • a protective panel or a touch panel is directly bonded to a display body as a method of simultaneously satisfying the reduction in visibility caused by an air layer and the reinforcement of the display body.
  • a sheet-like double-sided pressure-sensitive adhesive sheet (Patent Document 1) or a liquid resin is used. Further, the touch panel and the protective panel are bonded together in the same manner.
  • optical display devices that display 3D images (so-called 3D images) and 3D images (so-called 3D images) are increasing.
  • a double-sided pressure-sensitive adhesive sheet or a liquid resin is used for bonding optical component constituent members such as a display body, a protection panel, and a touch panel.
  • the protection panel light-shielding printing, touch panel flexibility and wiring, display panel wiring, black matrix and optical film Since energy rays are shielded, poor curing of the liquid resin is regarded as a problem.
  • thermosetting combined type reaction curable resin composition has been proposed (Patent Document 2) against such poor curing of the light shielding portion.
  • thermosetting combined type reaction curable resin composition of Patent Document 2 there is an upper limit (80 ° C. or lower) in the thermosetting temperature due to poor curing due to oxygen inhibition and compensation conditions of the optical film, so that a sufficient cured state is obtained. It may not be possible.
  • the size of the display body to be bonded with the energy ray curable liquid resin has been increasing year by year so that it can be performed from a mobile size to a monitor or TV size.
  • it requires a conveyor type or batch type area irradiation ultraviolet irradiation device that employs a metal halide light source or an LED light source, so that an increase in production equipment costs, an increase in line area, and an increase in UV process time are also problems. .
  • the problem to be solved by the present invention is that when producing an optical component by bonding an optical component constituent member via a reactive curable resin composition, the reactive curable resin composition is also used in a place where light does not reach. It is providing the manufacturing method of the optical component which can fully harden
  • the present invention includes the following.
  • the present invention (1) is an optical component manufacturing method in which an optical component component member A and another optical component component member B are bonded together via a reaction curable resin composition, and (1) the optical component configuration A step of disposing a coating composition containing a reaction initiator capable of initiating a polymerization reaction of the reactive curable resin composition on one or both of the opposing surfaces of the members A and B; (2) disposing on the surface Disposing the reactive resin composition on at least one surface of the coated composition and the surface on which the coating composition is not disposed, and (3) between the optical component components A and B. Bonding the optical component constituent members A and B so that the coating composition and the reactive curable resin composition are in contact with each other via the reactive resin composition, and (4) the reactive curing.
  • the polymerization reaction of the resin composition was initiated by the initiator, a method of manufacturing an optical component, which comprises a step of curing the reactive curable resin composition.
  • the present invention (2) is the method for producing an optical component of the present invention (1), wherein the reaction initiator is a compound capable of initiating the polymerization reaction of the reaction curable resin composition at 10 to 60 ° C.
  • the reaction curable resin composition includes an energy cleavage type initiator, and before the step (4), the reaction curable resin composition is formed by the energy cleavage type initiator. It is a manufacturing method of the optical component of this invention (1) or (2) including the process of starting a polymerization reaction.
  • This invention (4) is a manufacturing method of the optical component of this invention (3) whose said reaction initiator is not the said energy cleavage type initiator.
  • the reaction initiator is at least one compound selected from the group consisting of a radical generator, a cation generator, an anion generator and a polycondensation / polyaddition reaction initiator. (1) It is a method for manufacturing an optical component according to any one of (4).
  • the steps (1A) to (1B) in the step (1), the steps (1A) to (1B): (1A) a coating containing a reaction initiator on one or both of the opposing surfaces of the optical component components A and B Disposing a coating composition further comprising a resin curing agent selected from the group consisting of a thermosetting agent and a photoinitiator; and (1B) applying heat and / or irradiating energy rays.
  • the present invention (7) is the optical component manufacturing method according to any one of the present inventions (1) to (6), wherein the optical component component A is a display panel and the optical component component B is a protective panel.
  • the present invention (8) is an adhesive composition kit for the method of manufacturing an optical component according to any one of the present inventions (1) to (7), which reacts with the coating composition defined in the present invention (1).
  • the present invention (9) is a coating composition as defined in the present invention (1) for the adhesive composition kit of the present invention (8).
  • the present invention (10) is an optical component produced by the method of any one of the present inventions (1) to (7).
  • the present invention (11) is an optical display device including the optical component of the present invention (10).
  • the reaction curable resin composition when an optical component is manufactured by bonding an optical component constituent member through a reaction curable resin composition, the reaction curable resin composition is sufficiently cured even in a location where light does not reach.
  • the manufacturing method of the optical component which can be provided, the adhesive composition kit used for the manufacturing method of the said optical component, and the coating composition which comprises the said adhesive composition kit can be provided.
  • the manufacturing method of the present invention is a method of bonding an optical component constituent member A and another optical component constituent member B through a reaction curable resin composition, (1) Disposing a coating composition containing a reaction initiator capable of initiating a polymerization reaction of a reactive curable resin composition on one or both of the opposing surfaces of the optical component constituent members A and B; (2) disposing a reactive resin composition on at least one surface of the surface of the coating composition disposed on the surface and the surface on which the coating composition is not disposed; (3) A process of bonding the optical component constituent members A and B so that the coating composition and the reactive curable resin composition are in contact with each other through the reactive resin composition between the optical component constituent members A and B. And (4) starting a polymerization reaction of the reaction curable resin composition with a reaction initiator to cure the reaction curable resin composition.
  • the reaction curable resin composition and the coating composition are separated and arranged, and in the step (3), the optical component constituting member A and In the step (4), the reaction curable resin composition is reacted with the reaction initiator in the coating composition while compressing the reaction curable resin composition and the coating composition so as to be in direct contact with each other. It is characterized in that the polymerization reaction of the product is started and cured.
  • the reaction initiator diffuses into the reactive curable resin composition layer, and the process (4) It is considered that the polymerization reaction proceeds at a temperature near the room temperature described above.
  • the reaction curable resin composition is formed even in a place where light does not reach by taking a curing mode in which the curing reaction of the reaction curable resin composition is initiated by the reaction initiator.
  • the object can be fully cured.
  • damage to a display body such as a liquid crystal display body can be greatly reduced as compared with a conventional method of curing a reaction curable resin composition by only irradiation with energy rays.
  • a display constituent member having a coating containing a reaction initiator is obtained.
  • the optical component constituting members A and B are not particularly limited as long as they are members constituting the optical component, and include a protective panel, a touch sensor panel, a display body, and a 3D system (parallax barrier glass, parallax barrier film, parallax barrier LCD, lens unit). ) And the like.
  • These optical component constituent members A and B may be transparent plates or may have a light shielding portion formed by light shielding ink.
  • the light-shielding ink may be a known light-shielding ink, and examples thereof include water-based inks, solvent-type inks, thermosetting inks, and energy ray-curable inks.
  • the light shielding portion refers to a portion where light does not reach, for example, that can be formed by the display panel or the touch sensor panel under the light shielding ink of the protective panel or by the display body or the light shielding ink of the touch sensor panel. .
  • the coating composition may be disposed in the light shielding portion.
  • “the coating composition is disposed on the light shielding portion” means that the coating composition is disposed only on the surface of the light shielding ink layer (for example, FIG. 4 (1)) or the light shielding ink layer is disposed.
  • the coating composition is disposed only on the surface of the optical component constituent member that is not formed and on which the light shielding portion is formed by the light shielding ink layer disposed on the other optical component constituent member (for example, FIG. 4). (2) and (3)).
  • the coating composition may be disposed only on the surface where the light shielding ink layer is not disposed, only on the light shielding portion, and on the surface where the light shielding portion and the light shielding ink layer are not disposed.
  • reaction initiator examples include reaction initiators according to the reaction mode of the reaction curable resin composition used in the step (2) described later. Specifically, the reaction initiator mentioned later is mentioned.
  • the coating composition is disposed on one or both of the opposing surfaces of the optical component components A and B.
  • the coating composition is preferably disposed on both surfaces of the optical component constituent members A and B facing each other.
  • Step (1) may be performed inline or off-line with respect to the optical component production line.
  • the amount of the coating composition to be arranged is preferably 0.001 to 100 g / m 2 , more preferably 0.005. ⁇ 10g / m 2, still more preferably 0.01 ⁇ 1.00g / m 2.
  • the coating composition may be disposed by applying a liquid coating composition.
  • the coating composition can be cured by evaporating the solvent contained in the coating composition by drying.
  • step (1) the liquid coating composition is further added with a resin curing agent selected from the group consisting of a thermosetting agent and / or an energy ray initiator, and after the coating composition is disposed by coating,
  • the coating composition may be cured by and / or energy rays. That is, step (1) is performed in steps (1A) and (1B):
  • thermosetting agent and energy beam initiator in the step (1A) examples include the compounds described below.
  • the resin curing agent used in the step (1A) may be used for curing the coating composition, or may be used for curing both the coating composition and the reaction curable resin.
  • the condition for curing the coating composition by applying heat is not particularly limited as long as the polymerization reaction of the reactive curable resin contained in the coating composition proceeds at a temperature and time.
  • heat is applied at a temperature of 60 to 200 ° C., more preferably 80 to 160 ° C., preferably 10 seconds to 24 hours, more preferably 0.1 to 12 hours.
  • the conditions for curing the coating composition by irradiating energy rays are not particularly limited.
  • the integrated light amount is preferably 50 to 3,000 mJ / cm 2 , more preferably 50. It is ⁇ 2,000 mJ / cm 2 , more preferably 50 to 1,000 mJ / cm 2 .
  • energy rays include electron beams, X-rays, ultraviolet rays, electron beams having high energy such as visible light in a low wavelength region, or electromagnetic waves, but ultraviolet rays are preferable because of the simplicity and widespread use of ordinary devices.
  • Step (2) is a step of disposing a reactive resin composition on at least one surface of the surface of the coating composition disposed on the surface and the surface on which the coating composition is not disposed.
  • the method of arranging the reaction curable resin composition includes a dispensing method and a coater method.
  • the amount of the reaction curable resin composition is preferably 10 to 1000 ⁇ m, more preferably 25 to 25 ⁇ m.
  • the thickness is 500 ⁇ m, more preferably 50 to 300 ⁇ m.
  • An energy-cleavable initiator is included in the reaction-curable resin composition used in the step (2), and the energy-cleavable resin composition is irradiated with energy rays before the step (4). If the initiator reaches the range where the light reaches by polymerization reaction and is cured, the bonded optical component system is physically stabilized, and the polymerization reaction by the reaction initiator in the coating composition in the step (4) This is preferable because it is performed in a stable environment.
  • the reaction curable resin composition contains an energy cleavage type initiator.
  • the reaction that proceeds with the reaction initiator and the reaction curable resin composition contained in the coating composition is in contact with each other, and the portion irradiated with light is the reaction curable resin composition.
  • the reaction of the reaction-curable resin proceeds by the energy-cleavable initiator contained in the.
  • the reaction initiator contained in the coating composition used in step (1) is not an energy cleavage type initiator.
  • Examples of the energy ray irradiation conditions include those exemplified in the step (1B) including preferred ones.
  • the optical component constituent members A and B are disposed so that the coating composition and the reactive curable resin composition are in contact with each other through the reactive resin composition between the optical component constituent members A and B. It is a process of bonding. Thereby, the bonded body of optical component structural members A and B is obtained.
  • the coating composition and the reaction curable resin composition are brought into contact with each other.
  • a means such as compression may be used to promote contact between the reaction curable resin composition and the coating composition.
  • Step (4) is a step of curing the reaction curable resin composition by initiating a polymerization reaction of the reaction curable resin composition with a reaction initiator.
  • the reaction initiator is diffused into the reaction curable resin composition layer by leaving the bonded body of the optical component constituent members A and B obtained in the step (3), and the polymerization reaction is caused. Progresses.
  • Such conditions are not particularly limited as long as the temperature and time allow the polymerization reaction of the reaction curable resin composition to proceed.
  • the reaction curable resin composition can be cured by initiating a polymerization reaction with a reaction initiator in the coating composition.
  • a coating composition when a coating composition is arrange
  • the curing reaction of the reaction curable resin proceeds by the energy cleavage type initiator contained.
  • the conditions of irradiation with energy rays include those exemplified in the above step (1B).
  • the manufacturing method of the present invention since the resin composition has been applied directly to the place where the step is generated, the thickness unevenness of the resin composition has occurred, but the printing step and the polarizing plate step are filled with the coating composition. Therefore, display unevenness caused by the difference in the bonding thickness can be solved. Furthermore, the coating of the end portion of the polarizing plate can suppress chemical cracks that are likely to occur with uneven thickness of the resin composition.
  • the coating composition of the present invention will be described.
  • the coating composition contains a reaction initiator capable of initiating a polymerization reaction of the reaction curable resin composition.
  • reaction initiator examples include a radical generator, a cation generator, an anion generator, and a polycondensation / polyaddition reaction initiator.
  • the reaction initiator can be used according to the polymerization reaction mode of the reaction curable resin composition.
  • the reaction curable resin composition is a radical reaction curable resin composition, a radical generator, and when the reaction curable resin composition is a cation reaction curable resin composition, a cation generator, a reaction curable resin
  • an anion generator is used.
  • reaction curable resin composition is a polycondensation / polyaddition reaction curable resin composition
  • a polycondensation / polyaddition reaction initiator is used. can do.
  • the complexing agent that forms the metal complex includes phosphoric acid such as acetylacetone, acetoacetate ester, carboxylic acid, alkoxide, amine compound, amide compound, hydroxymate acid, ketone compound, imine compound, thiol compound, and dibutyl phosphate. Examples include esters.
  • acetylacetone vanadyl manufactured by Nippon Kagaku Sangyo Co., Ltd .: Nasemuvanadil
  • Nasemuvanadil which is a complex of acetylacetone and vanadium
  • vanadium oxytriisobutoxide manufactured by Nichia Chemical
  • a radical generator may be used independently and 2 or more types may be used together.
  • Cation generators include ionic photoacid generators such as aryldiazonium salts, diarylhalonium salts, triarylsulfonium salts, triphosphonium salts, iron allene complexes, titanocene complexes, and arylsilanol aluminum complexes; nitrobenzyl esters, sulfonic acids
  • Nonionic photoacid generators such as derivatives, phosphoric acid esters, phenol sulfonic acid esters, diazonaphthoquinone, N-hydroxyimide sulfonates and the like. These may be used independently and 2 or more types may be used together.
  • Anion generators include 1,10-diaminodecane, 4,4′-trimethylenedipiperazine, carbamates and derivatives thereof, cobalt-amine complexes, aminooxyiminos, ammonium borates, tertiary amines, imidazole And the like. These may be used independently and 2 or more types may be used together.
  • polycondensation / polyaddition reaction initiator examples include metal catalysts such as triphenylphosphine, amines, imidazole, pyridine, isocyanate compounds, titanium, aluminum, germanium, and platinum. These may be used independently and 2 or more types may be used together.
  • metal catalysts such as triphenylphosphine, amines, imidazole, pyridine, isocyanate compounds, titanium, aluminum, germanium, and platinum. These may be used independently and 2 or more types may be used together.
  • the reaction initiator is preferably a compound capable of initiating the polymerization reaction of the reaction curable resin composition at 10 to 60 ° C.
  • examples of such compounds include metal oxides such as iron (Fe), cobalt (Co), copper (Cu), zinc (Zn), vanadium (V), zirconium (Zr), and titanium (Ti), and the metal An isocyanate compound; an aliphatic amine; a polyamide resin; a tertiary amine; a polyamine; a polymercaptan; a Lewis acid and its amine complex; and a platinum catalyst.
  • the amount of the reaction initiator is preferably 0.01 to 80% by weight, more preferably 0.1 to 50% in the coating composition from the viewpoint of sufficiently effecting the reaction curable resin composition in the step (4). % By weight, more preferably 1-30% by weight.
  • the coating composition may contain further components within the scope of the object of the present invention.
  • the coating composition is not particularly limited as long as it is a composition that can coat the surface of the optical component constituent member.
  • the coating composition can include a solvent.
  • an organic compound or an inorganic compound that is considered to be capable of forming a film of a monomolecular film or more on the surface of the optical component constituting member is preferable.
  • solvents that are organic compounds alcohols such as ethanol and 2-propanol; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, and isophorone; ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether Ethers and acetals such as propylene glycol monomethyl ether acetate; esters such as ethyl acetate and butyl acetate; hydrocarbons such as cyclohexane, benzene, toluene and xylene; allyl bromide, benzyl bromide, benzyl chloride, carbon tetrachloride Halogenated hydrocarbons such as dichloromethane, chloroform; N, N-dimethylformamide, N-methylpyrrolidone, dimethylsulfoxide, etc. It is below. Examples of
  • GLS-HF000 MEDIUM made by Teikoku Ink Manufacturing Co., Ltd., polyester resin
  • DS-HF10929 TKI MEDIUM made by Teikoku Ink Manufacturing Co., Ltd., acrylic polyol resin
  • TE-2000 made by Nippon Soda Co., Ltd., polybutadiene resin
  • Light ester HO-250 manufactured by Kyoei Chemical Co., Ltd.
  • QM-657 manufactured by
  • Resin may be reactive or non-reactive with respect to heat and energy ray irradiation.
  • the resin that is reactive to heat and energy ray irradiation include a reactive curable resin used in a reactive curable resin composition described later.
  • the coating composition contains a resin that is reactive to heat and energy ray irradiation.
  • the amount of the resin in the coating composition is preferably 10 to 99.99% by weight, more preferably 20 to 80% by weight, and further preferably 30 to 60% by weight.
  • the coating composition may contain a resin curing agent selected from the group consisting of a thermosetting agent and a photoinitiator.
  • a coating composition contains a thermosetting agent and a photoinitiator, it is preferable to contain a cation reaction curable resin, a radical curable resin, and an anion curable resin further.
  • these reactive curable resins include resins exemplified in the reactive curable resin composition.
  • thermosetting agents diphenyliodonium hexafluorophosphate, diphenyliodonium hexafluoroantimonate, diphenyliodonium tetrafluoroborate, diphenyliodonium tetrakis (pentafluorophenyl) borate, bis (dodecylphenyl) iodonium hexafluorophosphate, bis (Dodecylphenyl) iodonium hexafluoroantimonate, bis (dodecylphenyl) iodonium tetrafluoroborate, bis (dodecylphenyl) iodonium tetrakis (pentafluorophenyl) borate, 4-methylphenyl-4- (1-methylethyl) Phenyliodonium hexafluorophosphate, 4-methylphenyl-4- (1-methylethyl) Phenyl
  • thermosetting agent examples include DS-HF 10929TKI CATALYST (manufactured by Teikoku Ink Manufacturing Co., Ltd., melamine resin).
  • the amount of the thermosetting agent is preferably 0.01 to 80 parts by weight, more preferably 0.1 to 60 parts by weight with respect to 100 parts by weight of the total of the curable resin, and 1 to 50 parts by weight. More preferably, it is part.
  • 2,6-dimethylbenzoyldiphenylphosphine oxide 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,6-dichlorobenzoyldiphenylphosphine oxide, and 2,6-dimethoxybenzoyldiphenylphosphine
  • Acylphosphine oxides such as fin oxide; Acylphosphine esters such as 2,4,6-trimethylbenzoylphenylphosphinic acid methyl ester; 4- (2-hydroxyethoxy) phenyl (2-hydroxy2-2propyl) ) Ketone, 2,2-dimethoxy-1,2-diphenylethane-1-one, 2-methyl-1,4- (methylthio) phenyl-2-morpholinopropan-1-one, 1-phenyl-2-hydroxy -2-methyl group Acetophenone series such as pan-1-one, 1-hydroxycyclohexyl-phenylketone, 4-diphenoxydichloroaceto
  • the amount of the photoinitiator is preferably 0.001 to 50 parts by weight, more preferably 0.01 to 20 parts by weight, and more preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the curable resin. More preferably, it is part.
  • the coating composition further includes a surfactant and a silane coupling agent for improving wettability to the surface of the optical component component, and a film forming agent for forming a film on the surface of the optical component component. It is preferable.
  • surfactant examples include an anionic surfactant, an amphoteric surfactant, and a nonionic surfactant. These can be used alone or in combination of two or more.
  • anionic surfactant soap, lauryl sulfate, polyoxyethylene alkyl ether sulfate, alkylbenzene sulfonate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkylphenyl ether phosphate, N-acyl amino acid salt, ⁇ -Olefin sulfonates, alkyl sulfates, alkyl phenyl ether sulfates, methyl taurates and the like.
  • An anionic surfactant can be used 1 type or in combination of 2 or more types as appropriate.
  • Amphoteric surfactants include alkyldiaminoethylglycine hydrochloride, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, lauryldimethylaminoacetic acid betaine, coconut oil fatty acid amide propyl betaine, fatty acid alkyl betaine, sulfobetaine And amidoxide. Amphoteric surfactants can be used alone or in combination of two or more.
  • Nonionic (nonionic) type surfactants include polyethylene glycol alkyl ester type compounds, alkyl ether type compounds such as triethylene glycol monobutyl ether, ester type compounds such as polyoxysorbitan ester, alkylphenol type compounds, fluorine type compounds, And silicone type compounds.
  • Nonionic (nonionic) type surfactants can be used singly or in appropriate combination of two or more.
  • silane coupling agents vinyltrimethoxysilane, vinyltrichlorosilane, vinyltriethoxysilane, methyltrimethoxysilane, methyltriethoxysilane, methyltriisopropoxysilane, ethyltriethoxysilane, etoltributoxysilane, cyclohexyltriethoxysilane Trialkoxysilanes such as phenyltriisopropoxysilane; tetramethoxysilane, tetraethoxysilane, tetrapropoxysilane, tetraisopropoxysilane, tetrabutoxysilane, dimethoxydiethoxysilane, dimethoxydiisopropoxysilane, diethoxydiisopropoxy Tetraalkoxysilanes such as silane and diethoxydibutoxysilane; dimethyldimethoxysilane, dimethyldiethoxysilane
  • a film formation agent Preferably it is a silicone type additive, an acrylic type leveling agent, a wax type surface conditioner, and a fluorine type surface modifier. More preferred are silicone additives, acrylic leveling agents, and fluorine surface modifiers, and more preferred are acrylic leveling agents and fluorine surface modifiers. Specific examples of such a film forming agent include lauryl acrylate.
  • the amount of the surfactant, the silane coupling agent, and the film forming agent is preferably 0.01 to 20% by weight, more preferably 0.1 to 10% by weight, and further preferably 0.1 to 10% by weight in the coating composition. 5% by weight.
  • reaction curable resin composition The reaction curable resin composition of the present invention will be described.
  • the reaction curable resin composition include a radical reaction curable resin composition, a cation reaction curable resin composition, an anion reaction curable resin composition, a polycondensation / polyaddition reaction curable resin composition, and the like.
  • a radical reaction curable resin composition is preferable from the viewpoint of curing with energy rays and reactivity with a reaction initiator in the coating composition.
  • radical reaction curable resin used in the radical reaction curable resin composition examples include (meth) acrylic resins, silicone resins, unsaturated polyester resins, and vinyl ester resins. Preferred are (meth) acrylic resins, silicone resins, and vinyl ester resins, and more preferred are (meth) acrylic resins.
  • the (meth) acrylic resin specifically, (meth) acrylate compounds such as dicyclopentenyloxyethyl (meth) acrylate and 2-hydroxybutyl (meth) acrylate; polyisoprene (meth) acrylate, polybutadiene ( Examples include (meth) acrylate-modified oligomers such as (meth) acrylate.
  • Examples of the cation reaction curable resin used in the cation reaction curable resin composition include epoxy resins, oxetane compounds, vinyl ether resins, and polystyrene resins. An epoxy resin and an oxetane compound are preferable.
  • anion reaction curable resin used in the anion reaction curable resin composition examples include epoxy resins, (meth) acrylic resins, cyanoacrylate resins, oxetane compounds, polystyrene resins, and polyethylene resins.
  • An epoxy resin, a (meth) acrylic resin, a cyanoacrylate resin, and a polystyrene resin are preferable, and a cyanoacrylate resin and a polystyrene resin are more preferable.
  • Examples of the polycondensation reaction curable resin used in the polycondensation / polyaddition reaction curable resin composition include polyamide resins, polyimide resins, polyester resins, polycarbonate resins, and silicone resins. Polyamide resins, polyester resins, polycarbonate resins, and silicone resins are preferable, and polyester resins, polycarbonate resins, and silicone resins are more preferable.
  • An energy-cleavable initiator can be included in the reaction-curable resin composition.
  • the energy-cleavage type initiator the above-mentioned photoinitiator can be mentioned.
  • examples of the resin contained in the reaction curable resin composition include acrylic resins, epoxy resins, and silicone resin compositions.
  • the amount of the energy-cleavable initiator is not particularly limited, but examples include the amount of the photoinitiator described above.
  • it is preferable that the reaction initiator contained in the coating composition is not the energy cleavage type initiator contained in the reaction curable resin composition.
  • the reaction curable resin composition contains a heat / light stabilizer from the viewpoint of optical transparency stability.
  • Heat and light stabilizers include hindered phenol antioxidants, phosphorus processing heat stabilizers, hydroxylamine processing heat stabilizers, benzotriazole UV absorbers, triazine UV absorbers, hindered amine light stabilizers, And benzoate-based ultraviolet absorbers.
  • Preferred are hindered phenol antioxidants, phosphorus processing heat stabilizers, and hindered amine light stabilizers, and more preferred are hindered phenol antioxidants.
  • the hindered phenol-based antioxidant specifically, pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl] propionate), 2,2-methylene-bis (4-methyl-6-tert-butylphenol), catechol, picric acid, tert-butylcatechol, 2,6-di-tert-butyl-p-cresol, and 4,4′-thiobis [ethylene (oxy) (carbonyl ) (Ethylene)] bis [2,6-bis (1,1-dimethylethyl) phenol].
  • Irganox 1010 I'nox 1010
  • BASF a commercial product.
  • the amount of the heat / light stabilizer is preferably 0.001 to 10% by weight, more preferably 0.01 to 5% by weight, and still more preferably 0.1 to 10% by weight with respect to the reaction curable resin composition. ⁇ 3% by weight.
  • reaction curable resin composition when mixed with the energy ray curable liquid resin composition in the absence of energy rays, radicals, cations or anions are generated at a temperature of 60 ° C. or less, and the reaction curable resin composition is It is preferable to include a compound to be cured.
  • Examples include organic peroxides (eg cumene peroxide, ketone peroxide, peroxyketal, hydroperoxide, dialkyl peroxide, diacyl peroxide, peroxyester, peroxydicarbonate), polyamines, acid anhydrides ( Phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, etc.), aromatic amine, hydrazide, amine adducts, dicyandiamide, polysulfide resin, Lewis acid (boron trifluoride, zinc chloride, aluminum chloride, iron chloride, tin chloride) ), Azo compounds (azobisisobutyronitrile, 1,1′-azobis (cyclohexanecarbonitrile), etc.), acids (organic acids or sulfonium salt-based acid generators that generate acid by low-temperature heating, etc.), bases (Polyamines such as aliphatic polyamines Amine compounds such as imidazole, hydrazide and
  • Adhesive resin composition kit Since the coating composition and the reaction curable resin composition are used in combination in the production method of the present invention, the coating composition and the reaction curable resin composition are used as an adhesive resin composition kit for the production method of the present invention. Configure.
  • the suitable coating composition and the suitable reactive curable resin composition already mentioned is appropriately selected according to the mode of the polymerization reaction using the reactive curable resin composition and the reaction initiator, The following combinations are more preferred.
  • the adhesive resin composition kit preferably contains an acrylic resin as a reaction curable resin and further contains an organic peroxide as a radical generator, and a reaction initiator, for example, , Iron (Fe), aluminum (Al), cobalt (Co), manganese (Mn), tin (Sn), zinc (Zn), vanadium (V), chromium (Cr), zirconium (Zr), indium (In)
  • a coating composition containing a metal such as titanium (Ti) or a complex of these metals or a reactive curable resin composition containing an epoxy resin as a reactive curable resin, and an acid as a reaction initiator And / or a combination with a coating composition containing a base.
  • Examples of the acid include an organic acid or a sulfonium salt-based acid generator that generates an acid by heating or light.
  • Examples of the base include amine compounds such as polyamine, imidazole and hydrazide, and compounds in which an amine compound is generated by heat or light.
  • the amount of the coating composition and the reactive curable resin composition in the adhesive resin composition kit is not particularly limited as long as the ratio of the reaction initiator in the coating composition to the curable resin in the reactive curable resin composition is satisfied.
  • the coating composition is preferably 0.01 to 100 parts by weight and more preferably 0.1 to 10 parts by weight with respect to 100 parts by weight of the reaction curable composition.
  • the manufacturing method of the present invention includes bonding a protective panel and a touch sensor panel, bonding a protective panel and a display, bonding a touch sensor panel and a display, touch sensor panel with protective panel and display Bonding of protective panel and display with touch sensor 3D system and bonding of display body, bonding of protective panel and display with 3D system, bonding of touch sensor panel and display with 3D system, It is used for bonding optical component components such as bonding of a touch panel with a protection panel and a display body with a 3D system, and bonding of a protection panel and a display body with a 3D system with a touch sensor.
  • the optical component obtained by the manufacturing method of the present invention is a bonded body of the optical component constituent members mentioned above.
  • a liquid crystal display and an organic EL display are mentioned as an optical display apparatus containing the optical component obtained with the manufacturing method of this invention.
  • Coating compositions a to d having the compositions (parts by weight) shown in Table 1 were prepared. The adjustment conditions are as follows: 3 g of reaction initiator, 0.5 g of monomers, and 100 g of ethanol are placed in a glass bottle with a capacity of about 200 ml, capped and manually shaken and stirred at room temperature (25 ° C.). Was dissolved to obtain 103.5 g of a coating composition.
  • Nasemu vanadil Natural Chemical Industry Co., Ltd .; vanadyl acetylacetonate
  • FC4430 manufactured by Sumitomo 3M; fluorinated surfactant
  • KBM1003 Shin-Etsu Chemical Co., Ltd .; vinyltrimethoxysilane
  • LA Kyoeisha Chemical Co., Ltd .; lauryl acrylate
  • reaction curable resin composition A having the composition (parts by weight) shown in Table 2 was prepared. Put 40g of UC-203, 40g of QM-657 and 13g of HOB into a Nangko container with a capacity of about 200ml, mix at room temperature (25 ° C) with a three-one motor (manufactured by Shinto Kagaku), and add I-184 to it. 3 g, 1 g of lucillin TPO and 1 g of I'nox1010, heated to about 60 ° C. in an oven and dissolved, then returned to room temperature, then 2 g of kayakmen H was added and a three-one motor (at 25 ° C.) 100 g of reaction curable resin composition A was obtained.
  • each of the coating compositions a to d was coated on the front surface of a glass substrate (50 ⁇ 40 ⁇ 0.7 mm) and dried at room temperature for 10 minutes to obtain a glass substrate with a coating composition.
  • a glass substrate with a coating composition and glass are bonded to each other with a thickness of 200 ⁇ mt using the reactive curable resin composition A so that the coating composition layer is on the inside, and then predetermined. It was allowed to stand at room temperature for 1 hour or 24 hours, and the cured state of the reaction curable resin composition A was confirmed by palpation according to the following criteria. When the liquid was not fluid by palpation, it was cured, and when it was fluid, it was uncured. The results are shown in Table 3.
  • Coating composition 2 Coating compositions ei having the composition (parts by weight) shown in Table 4 were prepared. 10 g of reaction initiator, specified weight of oligomer, monomers, and their curing agents are placed in an approximately 200 ml glass bottle and stirred at room temperature (25 ° C.) to dissolve the reaction initiator and the like to form a coating composition. Obtained.
  • Nasemu vanadil (Nippon Chemical Industry Co., Ltd .; vanadyl acetylacetonate) GLS-HF000 MEDIUM (made by Teikoku Ink Manufacturing Co., Ltd .; polyester resin) DS-HF 10929 TKI MEDIUM (manufactured by Teikoku Ink Manufacturing Co., Ltd .; acrylic polyol resin) TE-2000 (Nippon Soda Co., Ltd .; polybutadiene resin) LIGHT ESTER HO-250 (N) (manufactured by Kyoeisha Chemical Co., Ltd .; 2-hydroxyethyl methacrylate) QM-657 (Rohm and Haas; dicyclopentenyloxyethyl methacrylate) DS-HF 10929 TKI CATALYST (manufactured by Teikoku Ink Manufacturing Co., Ltd .; melamine resin) I-184 (manufactured by BASF; 1-hydroxycyclo
  • each of the coating compositions e to i is coated on the front surface of a glass substrate (50 ⁇ 40 ⁇ 0.7 mm), and the coating compositions e, f, g, and i are thermally cured at 150 ° C. for 30 minutes to be coated.
  • the composition h was UV-cured with a metal halide lamp with an integrated light amount of 3,000 mJ / cm 2 to obtain a glass substrate with a coating composition.
  • a glass substrate with a coating composition and glass are bonded to each other with a thickness of 200 ⁇ mt using the reactive curable resin composition A so that the coating composition layer is on the inside, and then predetermined.
  • Optical component component A 2 Light-shielding ink layer 3: Energy ray curable resin composition 4: Coating composition 5: Optical component component B 6: Curing part of energy ray curable resin composition 7: Part where reaction curable resin composition is cured by contact with compound capable of curing reaction curable resin composition in coating composition 8: UV 9: UV cured part

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JP6829219B2 (ja) * 2018-03-12 2021-02-10 株式会社飯沼ゲージ製作所 貼り合せ方法及び貼り合せ装置
KR102058865B1 (ko) 2018-04-12 2019-12-24 (주)아이엠 초가속 열소재를 이용한 발열 디바이스 및 이의 제조방법

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CN112706433A (zh) * 2019-10-25 2021-04-27 阳程科技股份有限公司 软性元件表面自动化成形异形光学胶脂的方法
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